Unsaturated organic compounds are useful compounds as medicines, agrichemicals, liquid crystal materials, organic EL materials and synthetic intermediates thereof, and among them, the demand for compounds having a biaryl structure is increasing. As the method for producing an unsaturated organic compound having a biaryl structure, a method of coupling a aryl halide with a boron compound using a palladium catalyst or a nickel catalyst has been known. Especially, from the viewpoint that a nickel catalyst is cheaper, a development of a coupling reaction using a nickel catalyst is desired industrially.
For example, Tetrahedron Letters, 1999, 40, 2323-2326 discloses a coupling reaction of an arylboric acid and an aryl chloride using NiCl2(dppe) catalyst.